What I get is a lot of survivor bias. "This is how to do it because this worked for me". What about all the people still in the middle of the pack in the gentlemen's race? Do none of them desire a top-ten finish?

I look at motivation as the hind-sight rationalization for how people got lucky. For all we know, 30 other people were trying what DHH was, but we never heard from them because they didn't get lucky.

I do think you can stack the cards in your favor (DHH is a really smart guy, that is certainly one planted card), but no amount of internal anything can guarantee success.

So I try to stack some cards: work regularly on my project, make a concerted effort to find value to add, interact with people in a positive way so I don't burn bridges, etc. Maybe it's not an "I can remake the world to be what I want" entrepreneurial attitude, but I think it is more realistic for a bootstrapped project.